


Man Up

by iwasanartist



Category: Castle
Genre: Crossdressing, Genderqueer, Other, Pegging, first time pegging
Language: English
Status: Completed
Published: 2013-08-28
Updated: 2013-08-27
Packaged: 2017-12-24 21:15:35
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 5,176
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/944738
Author URL: https://archiveofourown.org/users/iwasanartist/pseuds/iwasanartist
Summary: <blockquote class="userstuff">
              <p>Everyone at the 12th knows Jenny likes light, frilly dresses, makeup and strappy shoes, but only Kevin knows about her penchant for crossdressing. And when she comes home one day in a three-piece suit, he gets far more than he bargained for.</p>
            </blockquote>





	1. A Very Important Date

**Author's Note:**

> I intended this to just be PWP with cross-dressing and pegging, but then Kevin and Jenny had to go and have a fight and all these feelings about gender and the difficulties a relationship can have when one person is a little bit queer and the other is cis. But then there's porn.

Kevin got home abnormally early that day -- almost a full 20 minutes before his wife would be home -- changed out of his suit and decided it would be a night where he did something out of the ordinary.  
  
Stepping into the kitchen, he got to work. He loved a great many things about living with Jenny, but he couldn't lie -- a kitchen that was perpetually stocked with more than leftover takeout and beer was pretty close to the top of the list. Quickly, he scanned the refrigerator and pantry.  
  
Groud beef, onion, garlic, mushrooms -- the sauce itself would be canned, but there were plenty of ways to improve upon it -- and of course the staple ingredient: long strands of whole-wheat spaghetti.  
  
He was dicing the onion when she called to say she was running late at the cleaners and had just dropped the ground beef in a skillet when he heard the front door open.  
  
"Hey, babe, I'm in the kitchen," he called. She didn't answer, but he could hear the crinkling of the drycleaning and the unmistakable whoosh of the plastic-covered clothes being tossed over the back of a chair as she kicked the door closed. Moments later, he heard the shower running, and he turned his attention back to their dinner.  
  
The meat was nearly browned when two hands covered his eyes.  
  
"Guess who?"  
  
Kevin breathed deeply. The scent of his own Irish Spring body wash filled his nose. Officer Krause had given him a case as a gag gift one Christmas, and it was Jenny's go-to soap for those days when she wanted to "man up" as she called it.  
  
"My, Esposito, how you've changed," he said as he continued to blindly stir the meat. "You're supposed to eat the cake, you know." Her breath tickled his ear as she laughed. 'Alice in Wonderland' -- Alice's ADVENTURES in Wonderland, she would always correct -- had been her favorite story since she was a child, and any time he could work a reference, however obliquely, into a conversation, it always made her smile. Her hands moved down to wrap around his waist.  
  
"I want you to see something," she whispered into his ear before pulling away. When he turned to face her, she was across the kitchen, leaning on the table, and his jaw dropped.  
  
Any other day, it might have been the hair he noticed first. Her long locks were sheared away into a short cut that, styled differently, wouldn't look terribly out of place with one of her flowery summer dresses. But today, his eyes latched onto the gray men's three-piece suit.  
  
He'd seen her in drag before -- in fact, their first date after he proposed was to a Kings and Queens show ( "I said yes, but you should know about this before you say 'I do,'" she had said). But those other forays into her cross-dressing were usually limited to an oversized sports jersey with her hair swept under a ball cap or tucked into a leather jacket with a men's white T-shirt, jeans and a pair of biker boots. This was something else entirely.  
  
"I hope you don't mind," she said. "I had Mr. Wong do some extra work on that suit the loose dog at the park tore up. He couldn't fix it, he said. Not unless you wanted to be showing your socks off to the whole precinct..."  
  
Kevin was silent as she trailed off. Soon her cheeks began to flush and he could see a flash of red creep up her neck at the collar.  
  
"It's stupid," she said as she undid the jacket. "I don't know what I was thinking." She shrugged out of the jacket and hung it on the back of a kitchen chair. "God, my hair," she whispered, but Kevin had stopped listening. He could only stare at the gray vest that snugly wrapped itself around her body, the yellow tie that disappeared beneath it and the crisp white sleeves that stretched from shoulders to cuffs.  
  
The spatula clattered to the floor as something inside him snapped. It was only an intense fear of housefires that gave him the presence of mind to reach behind him and crank the dial of the burner to what he hoped was "off" before he went to her, reaching his destination in three strides, taking her in his arms and covering her mouth with his own as he kissed her deeply.  
  
"You look great," he breathed into her ear, far more turned on than he could ever hope to explain or understand. She looked up at him.  
  
"You really think so?"  
  
"I do," he said as he kissed her neck.  
  
"Good," she said as she pushed his shoulder, spinning him slightly before guiding him across the kitchen until his back met the wall. Along the way she hooked her shoe around the footstool he used to change the lightbulbs, slid it over and stepped atop it in one motion.  
  
The added height made her slightly taller than him, and she tilted his face to her, leaning down for a kiss that caressed his lips and tongue before moving to his neck. Her mouth was hot and wet as it traveled across his skin. His breaths came quick and shallow as he leaned his head back, giving her more taut canvas to explore from this new angle.  
  
His hands moved to the vest, expertly working its buttons until it was open. With one end of the fabric in each hand, he pulled her closer until her hands went to his wrists, stopping him.  
  
"There's something else," she whispered as she took his hands in hers. He gazed in her eyes, so beautiful and lusty but with just a touch of fear.  
  
"What?"  
  
She laid his hands on her sides, underneath the vest, and guided them down, over her waist and hips until they rested on her hips. Slowly, she brought them together until his thumbs and forefingers met at the front of her pelvis. He noticed the eerily familiar bump, then -- could feel it through the cloth of the trousers and shorts he knew she was wearing beneath.  
  
"Uh, Jenny," he said with a swallow. "Is that, ummm..."  
  
"I may have done some online shopping," she whispered as she moved his hands to her backside and leaned into him. Her mouth was back to his neck -- the opposite side this time -- but all he could feel was her new...addition...pressing itself into his own once-burgeoning erection. How had he missed it before?  
  
"So, are you -aaha" he began as she nibbled on his earlobe, "are you, uh, going to enter the drag contests?"  
  
"No," she said as she flicked her tongue across his adam's apple. "If it got out at the precinct...I could never do that to you..."  
  
"So, it's..." he closed his eyes and tried to keep his train of thought as her hands moved across his body. "It's just for you then. For when you want to-"  
  
"It's for us," she said. She was still kissing him, nuzzling his neck and sliding her hands over his body.  
  
"For us?" He said absently, his focus beginning to wane beneath her touch. She moved back to his ear, and he could feel her breath, hot against him.  
  
"I want to be inside you," she whispered.  
  
And then everything went cold.  
  
"You want to what-now?" he said, Perhaps he had misheard. She repeated herself, and Kevin could almost hear Richard Castle narrating the proverbial record-scratch.  
  
"I want to be inside you."  
  
"Okay," he said as he lifted her off the stool and set her feet back on solid ground, moment over. "This is where I get off the crazy-train."  
  
"Kevin!" She looked hurt and angry, but he ignored her. Stepping around her, he picked the spatula off the floor and tossed it into the sink before grabbing a beer from the refrigerator. She scoffed at him as her hands went to her hips.  
  
"So, what? Twenty seconds ago you were hot to go and now you're just going to drink a beer and fire up the old Xbox?"  
  
"What do you want from me?" Kevin asked as he twisted the cap off his drink. He tossed it toward the trash, but it bounced off the edge and skittered across the floor. "I think I've been pretty goddamn understanding of a lot of things, but you come home packing a - a - a PENIS under there," he said as he waved his hand in her direction, "And I'm supposed to be happy when you say you want to ram it up-"  
  
"Kevin Ryan don't get crude with me," she said harshly.  
  
" 'Don't get crude,' Are you...this is unbelievable," he muttered as he headed out of the kitchen.  
  
"I don't see what the big deal is!" she called after him. "I know you were with guys in college; we both experimented back then."  
  
"I made out -- with my roommate -- when we were both three sheets to the wind," he exclaimed as he turned back to face her. "THIS is completely different. Completely."  
  
Kevin stormed into the living room and sank onto the couch. The remote was next to him, and the videogame controller just a reach away, but he found himself staring blankly at the TV's dark screen while he listened to Jenny in the kitchen.  
  
The faucet ran -- he was pretty sure she was washing the spatula. Cabinets opened and closed as she tidied up, and the broom swished across the floor until his bottle cap had been retrieved -- it sounded like it had gotten stuck under the stove. He thought briefly that he should go help her, but his legs refused to move.  
  
Moments later she appeared, dropping onto the couch next to him, her own bottle in hand. There was only a cushion of space between them, but it may have been a mile. They sat in silence, both staring ahead save a few side-glances when each thought the other wasn't looking. At first, he looked at her hair and the way its new length framed her ear and showcased the long lines of her neck. But then his eyes traveled downward to the spot between her legs where he knew *it* was.  
  
"I'm sorry," she finally said. "I didn't mean to just blurt it out like that."  
  
"Oh, so there was a whole seduction plan," he replied, a hint of bitterness creeping into his voice. "Boy, I sure would've liked to know what THAT was."  
  
"Well, you know, what do you want from me, Kevin?" Her voice, too, betrayed the frustration of the evening. "Pardon me for getting distracted. All this time, and you've never come on to me like that before-"  
  
"That's because you've never been so hot before! -- Whoa, that did NOT come out right," he quickly added as she raised an eyebrow at him.  
  
"It's the vest," she said finally as the corner of her mouth ticked up in an amused half smile.  
  
"The what?"  
  
"Vests," she said again. "I told you they were sexy."  
  
They laughed. Not the deep belly-laughs of comedy, but rather the almost giggles of two people privy to an inside joke that had found its way 'round again. As their laughter died down, they bridged the gap between them, fingers mingling as they met at the middle cushion's center. And then there was silence again.  
  
"I don't understand," Kevin finally said. "I mean, how would...that...do anything for you when it's not real and you can't feel it?"  
  
Jenny coughed once before answering.  
  
"There are some 'strategically placed' nubs in the...in the harness," she said. "They're battery powered and remote controlled, so, you know. Plus, from what I hear, just the motion is kind of a mental high. But maybe you have to be really imaginative for that, I don't know."  
  
"Do you..." He paused, struggling to find words for a question he wasn't sure he wanted to ask. "Do you want it to be real?" he finally said. The question hung in the air, the possibilities of its answer almost painful between them.  
  
"I don't know," she answered. "A year ago I'd have said..." she trailed off as her voice began to shake. She swallowed once and when she spoke again her voice was steady. "Not always," she finally said. "But sometimes I wonder."  
  
He took another drink and the uncomfortable silence threatened to encroach again.  
  
"Baby, it's okay," she said before it could. "We don't..." She took a deep breath. "Maybe we can...we can just wipe tonight from the books, no harm, no foul. I mean, this isn't what you signed up for, I know."  
  
"But it's important to you?"  
  
"You're important to me." Untangling their fingers, she took his hand in hers and gave a gentle squeeze. "It's okay."  
  
A quietness filled the air. Not the uncomfortable silence that had hung previously, just a gentle, peaceful quiet. Neither had turned a light on, and the falling sun left a slight glow that was beginning to fade into a gray darkness. He watched her as she set her drink down and tugged at her tie. The knot traveled a few inches south and she undid a few buttons, loosening the collar of the white dress shirt. Arching her body and with one foot on the coffee table, she leaned back, resting her head on the back edge of their couch as the sun disappeared.  
  
"You better get to work," he said finally.  
  
"I'm sorry?"  
  
"Hey, I am not an easy lay," he said with a smile. "I require wining and dining -- maybe a little more wining..."  
  
She smiled as he spoke and scooted toward him.  
  
"Wining and dining," she whispered in his ear before drawing lazy circles with her tongue. One hand combed through his hair as the other came to rest on the fabric of his T-shirt, just over his heart.  
  
"Mm hmm," he answered. "And flowers would not be remiss."  
  
"Flowers," she repeated as she kissed the corner of his mouth and then his cheek. "I thought maybe I'd just do this," she said, pressing her lips firmly to that spot at the edge of his jaw, just beneath his ear.  
  
"Or that," Kevin groaned and pulled her onto his lap, her knees surrounding his hips. "That works, too." She leaned forward, pressing herself against him as her lips traveled up his neck and across his throat before finding purchase at his mouth.  
  
She leaned back, breaking the kiss, and her hands went back to the tie around her neck. Loosening it further, she had just begun to pull it over her head when he grabbed her wrists, pulling her hands toward him. He kissed her fingers, rolling his tongue over one that slipped past his lips. He watched as her eyes closed and her chest heaved with each breath. He released her, and moved to her neck, undoing the tie's knot with practiced hands. When it was smooth once more, he gently tugged the larger end and watched the smaller rise beneath her collar until it reached her shoulder, disappeared around her neck and finally came free in his own hands.  
  
She opened her eyes and reached for the free end, using it to draw them closer together. Their hands clasped and fingers curled around the  tie until they melted into one another and the strip of fabric fluttered to the floor.


	2. Through The Looking Glass

This wasn't the first time Kevin had seen Jenny in a state of undress on a gender-bending day. Several tight-fitting T-shirts usually hung in the back of their closet, and when layered together underneath yet another shirt, they generally did a fine job of making her look like an unusually tall, shapeless 12-year-old boy.  
  
Today was different.  
  
Today, he propped himself up on an elbow, already naked and draped with a sheet in their bed, and watched her disrobe. She stood before him, sockless but still in the trousers that used to be his, and removed the dress shirt, to reveal a single, sleeveless compression garment -- designed to look like any other men's undershirt -- that not only flattened her chest but provided the slightest bit of definition. Though he would be loath to admit it, the new piece of clothing actually gave her a more masculine look than some of the more indulgent men on the force.  
  
The biggest difference of the night, though, was yet to come. His eyes followed her hands as they traveled downward and she slipped out of the trousers and underwear. Kevin wasn't entirely sure what he had expected. Maybe some brightly-colored piece of dick-shaped plastic that would just, sort of, fold out and latch into place, somehow?  
  
What he did not expect was to be gazing at a hyper-realistic four-inch cock naturally hanging as if it had always been there. He watched as she grasped it with one hand as the other readjusted the straps that held it in place. It was soft and stretched slightly when she moved her hand. He frowned at it, entirely unsure of how it was supposed to function.  
  
"I have to do something, you know, to get it up," she said as if reading his mind.  
  
He shrugged and turned toward his bedside table -- downing his glass of red wine before pouring another. As he watched the last drops drip into his glass he could hear her rifling through a box, shuffling through god-knows-what and just in general making noise that made him glad they had decided to crack the expensive bottle. He drank that as well before turning back to her.  
  
She was watching him, eyes full of love and lust and nervousness.  
  
"What do you think?" Her new little friend was standing at attention.  
  
"That's...a penis..." was about all he could muster.  
  
"Thank you, Detective Obvious" she said with a slight smile.  
  
"You should see me at a crime scene. 'That's a footprint...Must be a clue!'"  
  
She smiled fully now, reached for a condom and tore open its wrapper. Kevin tried to treat everything as if it were normal. Nothing out of the ordinary here, officer, we're just two all-American kids getting it on within the bonds of holy matrimony. Everything is just fine. But as Jenny went to apply the condom, it slipped from her fingers, hitting the carpet with a bounce, and Kevin lost it. Maybe it was the wine, maybe it was the nerves, but he couldn't hold back the laughter that bubbled forth in a chittering stream.  
  
Soon she was laughing, too.  
  
"What do you expect," she said. "I've never done it from this perspective before."  
  
"Imagine how I feel," he said as he grabbed another condom from the nighstand and stood up. "Here, let me help."  
  
"Wait!" she held out a hand, and he froze in his tracks, watching her as she picked up a small bottle of perfume and spritzed it several times in the space between them. "Okay," she said, motioning him forward.  
  
He closed his eyes and stepped through the lingering haze. Lilacs. It was the same fragrance she had worn on their wedding day -- and their wedding night. One she saved for special occasions.  
  
He stood behind her and wrapped his arms around her waist. Opening the condom, he tossed the wrapper away and touched the circle of latex to her tip. She leaned into him as he pulled it over the shaft, and his hands came to rest at its base, palms lightly cupping a pair of half-spheres as his fingers came to rest between her legs, gently rubbing over cloth. She moaned, and Kevin could feel the familiar tightening in his groin as the blood in his body began the first stages of its mass redirect. He kissed her neck, breathing deeply and taking in her scent -- his scent. Their scent.  
  
She turned around in his arms. The movement was awkward and required more shifting than usual, but they made it work. She kissed him, tugging gently at his lower lip as she backed away, holding his hands and leading him to their bed.  
  
He sat at the edge, and she sat next to him, arms wrapped around him with the slick material of her shirt rubbing against his bare skin. She gave him a gentle nudge until they were both lying on the bed. She pressed a small device into his palm. It reminded him of a key fob for unlocking car doors, but of course, neither of them had a car.  
  
"What's this?" he asked.  
  
"Remember how I said it had a remote? That's it." _There are some 'strategically placed' nubs..._  
  
Kevin looked closely at it. There were three buttons -- a plus sign, a minus sign and power.  
  
"That one turns it on and off, and those two control instensity," she explained, taking it from his hand. "Three speeds: low, medium and high."  
  
"Why are you telling me this?"  
  
"I want you to have it," she answered softly as her tongue ran across his collarbone and up his neck, "to work it however you want. However you feel..." she paused, not sure how to explain or continue.  
  
"Okay," he said, taking it back from her and holding it loosely in his hand. "I get it."  
  
She smiled and kissed him, trailing more kisses across his neck before whispering into his ear "but maybe wait a few minutes..." her hand slid down his chest and grazing his sides before dancing over his stiffening cock. Her lips followed, circling his nipple, and tickling his ribs before her tongue dipped into his navel, swirled about and then continued south.  
  
Kevin lifted his head and watched as she went down on him, sliding her hot tongue over him before suckling his head. He leaned back, resting against a pillow. Closing his eyes, he let the sensation wash over him as her tongue curled around the bottom of his penis perfectly and slid around him with every movement she made. Her hand moved lower still, gently massaging him. She let him go, breathing deeply as she did. She slid off the bed now. His legs draped over her shoulders as her tongue flicked over that last bit of flesh separating his front and back.  
  
And with a final lick, she was gone. He could hear her as she flipped the cap off a tube of lubricant and squeezed. She was on him again, her hands sliding slickly from tip to base and beyond, following all his curves with gentle precision. He shifted his hips, exposing himself to her as she squeezed more lubricant from its tube. She ran her fingers between his cheeks, finally coming into contact with his opening. The pressure sent a shiver down his spine and she pulled back quickly.  
  
"Are you okay? Do we need to stop?" She was concerned for him, and if it were possible, it made him love her even more.  
  
"No, it's all right," he answered. If she wanted something special, he would try to let her have it. She reached a hand up to him, and he squeezed it reassuringly. "It's okay."  
  
She went back to work, and as one finger slipped ever-so-slightly inside of him he exhaled, staring at the ceiling. Breathe in. Breathe out. One breath after another. His eyes fluttered closed as she continued, adding another finger at one point, and it surprised him how not unpleasant it was to feel her like that.  
  
Soon her lips were on him again. She took all of him into her mouth, and lying there, with her inside him and around him, his thumb brushed across the button of her control. She sighed -- he could feel it at the back of her throat, and it elicited one from his as well -- as her harness hummed to life on its lowest setting.  
  
She backed away, pulling her hand free from him before leaning forward. He could feel her sheathed cock against his as she kissed him. He reached down, letting his fingers slide over both, and she moaned as they brushed her thigh.  
  
Breaking the kiss, she slid her tongue down his body until she was standing at the edge of the bed again. He shifted again, spreading his legs wide with his heels resting on the mattress. They could have tried any other number of positions discovered in what may well have been The Most Awkward Amateur Porn Search Ever -- but it wasn't them. It wasn't what they did. Jenny wanted to experience as best she could what it was like to be him when he was with her, not what it was like to be some muscle-bound jock screwing a faceless boy toy from behind. She wanted to see him. To feel him. To look into his eyes and know they would always be together.  
  
And so they would try this, both silently grateful for the couples yoga class they had taken early in their relationship as she positioned herself between his legs and guided the tip of her length into him.  
  
She was stiff and slow as she pushed forward and pulled away. If anything, the motions were more intrusive and less natural than preparing him for the moment had been. He looked at her and realized why. He'd seen that expression on her face before -- usually reserved for the Sunday crossword, picking china patterns and packing extraordinary amounts of clothes into extraordinarily small suitcases. It was concentration in its rawest form. Concentration as she actively tried not to move too fast, go too deep or even be too loud.  
  
Lightly he ran his fingers up her arm and caressed her cheek. As his thumb passed over her lip with a slight tug, he pressed another button. She gasped as an audible buzz filled the room and her knees buckled into the mattress. Kevin grunted as their angle changed abruptly. She got that look again -- that 'deer-in-the-headlights-what-have-I-done?!' expression -- and was about to jerk away again when he grabbed her arms.

Raising his head and chest -- thank you, yoga -- he kissed her, wrapped his arms around her and lowered her onto him. It was awkward and uncomfortable for a moment, but as they settled into this new position, chest to chest with arms tangled together and lips on lips, it was perfect.

She began to thrust with slow, rhythmic movements. When she moved into him, he could feel her faint thrum against his skin, disappearing as she pulled away. _There and gone. There and gone. There and gone._

Her pace began to quicken and sighs of contentment punctuated her breath with every thrust. He matched her, motion for motion and breath for breath. She called his name, the hot air tickling his neck as she leaned her forehead against him. With his legs wrapped around her, he could feel her thighs begin to tense, and he knew in that moment he needed her. He wanted her, more than he could stand.

He pressed her button a third time and she fell forward with a cry. Her body was flush with his, and he could feel her heavy vibrations inside and out and -- oh, god -- it was ecstacy as he came beneath her, his warmth spreading between them as his hand clenched onto the control, quieting it, until all that was left was the two of them, quivering against one another as they struggled to find breath and calm their racing hearts.

"I love you," she whispered, her face damp with sweat and tears she kissed his cheek. He nodded, still unable to find words to match his shaking breath as he briefly caught her lips in his. She smiled at him as she lifted her body off of his and slid her hands down his chest as she backed away. She gave him a few tender strokes as she pulled out of him, and a final wave of blinding, white-hot euphoria surged through Kevin's body.

He could hear her as she got ready for bed -- removing all the accoutrements that had made the night what it had been -- and was dimly aware of the damp cloth she ran across his body, but his thoughts were on her and how it felt to have her fill him up, body, mind, heart and soul.

The next morning, they would go to work. Jenny would wear a summer dress and field a wealth of compliments on her bold new haircut, and Kevin, in a yellow tie and still smelling faintly of lilacs, would receive a knowing yet wholly uninformed grin from Esposito as his partner gently ribbed him about the length of honeymoon phases.

And that night, they would make love, the same as they always had and the same as they would many more times in the course of their lives. But as weeks and months progressed, they would find themselves periodically drawn down the rabbit hole.

It wasn't always sexual. Sometimes they would just share a meal or watch a movie before bed. And sometimes, he would come home after a long day's work and find her in gym shorts and a T-shirt, curled up on the couch, manned up but asleep in the television's glow with one hand resting almost protectively against her body. If he could manage without waking her, he would pick her up, carry her to bed and lie with her back pressing against his chest and his arms wrapped around her until they were both asleep.

Other times they would steal away, going to a show or a club across town, far from the eyes of friends and colleagues. These interludes in public often found Jenny full of excitement and feeling amorous. And the more they were together, the more Kevin began to think of her acquisition not as a thing or a device or even a sex toy. It was just a part of her that he could no more deny than her eyes or her lips.

And so, when she asked him to go down her after a concert by a coverband of some rock group she loved in high school, he did without question or hesitation. There were no remotes that night -- just fingers, fevered imagination and his mouth, kissing her inner thigh as his tongue flicked across the crease of her leg before sliding up her length. She clutched at his hair, running her hands over everything in reach as she passed between his lips. She came into his hands with a whimper that night.

But that night and the many that would come before and after it were in the future. On this night, their first time exploring a new wonderland, all Kevin could think about as Jenny climbed into bed, as she pulled up a blanket to combat the chill that had set in during her absence, and as she snuggled next to him, the valley of her now bare breasts pressing into his side, was that they were -- in every way -- a perfect fit.


End file.
